Formaldehyde → HCID 22624037, compound

HRID 567044Notes

Reaction equation

HRID 567044 reaction equation
[OH:1][N:2]1[C:11](=[O:12])[C:10]2[CH:13]=[C:14]([OH:17])[C:15](Br)=[C:8]3[C:9]=2[C:4](=[CH:5][CH:6]=[CH:7]3)[C:3]1=[O:18].C=O.CN.[CH2:23]([N:25](CC)[CH2:26]C)C>O1CCOCC1>[OH:1][N:2]1[C:3](=[O:18])[C:4]2[C:9]3[C:8]([CH:7]=[CH:6][CH:5]=2)=[C:15]2[N:25]([CH3:26])[CH2:23][O:17][C:14]2=[CH:13][C:10]=3[C:11]1=[O:12]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 8471TriethylamineHCID 22623894HCID 22623894, compound

Product 1

HCID 22624037HCID 22624037, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 175 mg (0.57 mmol) of 2,5-dihydroxy-6-bromo-benzo[de]isoquinoline-1,3-dione (from Example 125) in 4 mL dioxane was added 0.6 mL (22 mmol) of 37% aqueous formaldehyde, 0.2 mL (2.32 mmol) of 40% aqueous methylamine, and 0.078 mL (0.57 mmol) of triethyl amine. The reaction mixture was stirred at room temperature for 220 hours and quenched with 20 mL water. The precipitate was isolated, washed with water, and dried to yield 50 mg of the title compound, mp 263-265° C.

Workup

  1. customquenched with 20 mL water
  2. customThe precipitate was isolated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-138ecc7ab62d493c8e4d30915cce889b
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

Loading…